Trichloroacetyl chloride → 2,2,2-trichloro-1-(4,5,6,7-tetrahydro-1H-indol-2-yl)ethanone

HRID 1411447Notes

Reaction equation

[NH:1]1[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[CH:3]=[CH:2]1.[Cl:10][C:11]([Cl:16])([Cl:15])[C:12](Cl)=[O:13]>ClCCCl>[Cl:10][C:11]([Cl:16])([Cl:15])[C:12]([C:2]1[NH:1][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[CH:3]=1)=[O:13]

Participants

Conditions

Temperature: 85 °C

Procedure

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer, condenser and nitrogen inlet was purged with nitrogen and charged with 4,5,6,7-tetrahydro-1H-indole (3.00 g, 24.8 mmol), trichloroacetyl chloride (13.5 g, 74.4 mmol) and 1,2-dichloroethane (50 mL). The solution was stirred at 85° C. for 2 h. After that time, the reaction mixture was concentrated under reduced pressure to afford a 100% yield (6.50 g) of 2,2,2-trichloro-1-(4,5,6,7-tetrahydro-1H-indol-2-yl)ethanone 101a as a black semi-solid: 1H NMR (500 MHz, DMSO-d6) δ 11.94 (s, 1H), 7.05 (s, 1H), 2.62 (t, 2H, J=6.0 Hz), 2.47 (t, 2H, J=6.0 Hz), 1.80 (m, 2H), 1.65 (m, 2H); MS (ESI+) m/z 266.0 (M+H)

Workup

customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer, condenser and nitrogen inlet
customwas purged with nitrogen
concentrationAfter that time, the reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-8490d00cdac04e6188845a68a1d057c6
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921353B2

Reaction notes

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